I’ve read the book a couple of times, and I’ve read other content around the topic of gaining context, but it’s something which has only just “clicked” for me as to why it’s so important. Also, after now understanding the importance of context, I’ve found it to be very difficult to actually practice.

The premise is quite clear as to how vital context is: Without context, we immediately jump in our heads to what we want to say next, based on the very first few words we hear from the other person. This is something I find myself doing far too frequently.

Most of us listen to someone with the intention of replying, and therefore as soon as we have a “reply” in mind, we stop listening and wait our turn to reply. No matter what remarkable new insights are uncovered in the subsequent words from the other person, it is likely that we now have a strong desire to share that initial thought we have about what to say back.

With context, on the other hand, we can achieve so much more. If we truly understand the background of the other person, we can tailor the approach for each occasion. I believe gaining or having context can be useful in so many scenarios:

A while back, I was in a Skype call with someone to try and help them with their current startup challenges.

As normal, I asked about the founder’s startup and what stage he was at. After uncovering a tiny amount of context about his previous experiences and where he was now at, I unfortunately slipped and switched to my own thinking about what the best next steps were for him.

I proceeded to advise him based on my previous experience. The experience I based my advice on was the following:

I had worked on an idea for a year and a half which I never charged for

I therefore generated no revenue, and consistently had to work on the side

While I had a few thousand users of traction, I failed to raise funding

I advised him to charge for his product from Day One, since that worked for me the after the first failure. I also advised him to aim for revenue and not worry so much about user numbers, since that’s what truly freed me from working on the side.

He was very receptive of my advice–even though it was the wrong advice for the situation he was in. Luckily, he went on to share extra information that changed everything:

He had a previous startup for which he had hundreds of paying customers and good revenues

He was still making money from the idea and had runway to last almost indefinitely working on a new idea

He got into an incubator with the idea

He went to the Valley to raise funding, but since he had low user numbers (even though they were all paying) he struggled to raise funding

I could now completely understand why, in fact, he shouldn’t just follow the advice I gave him. He had almost entirely the opposite previous experience to me, yet equally valuable and foundation building. He was perfectly poised to try an idea which could gain massive visibility rather than simply making money. Making some money was not his biggest challenge, as it was for me when I started.

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Our opposite contexts meant that in fact opposite choices for next steps made complete sense. I was genuinely taken aback when I realized this.

Practicing “searching for context” is something I’ve found to be very exciting. When you approach a conversation without any need to have the intent of replying, without any need to have a “smart” response, it changes the entire flow of the discussion.

Here are some of the things I’ve found very useful in trying to be focused on understanding the other person:

Give the other person your full attention

Whenever I have a call, or whenever I get dinner with someone, or when we have a team standup, I turn my phone over and try to adjust my posture to lean forward, into the conversation, and focus on hearing every single word. It can be a challenge, and sometimes my mind drifts, but with conscious effort to do this, I have found I can “train the muscle” and focus for longer.

Remember that you don’t need to respond

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I used to feel that I always had to respond if there was the slightest moment of silence between myself and someone I was speaking with. This assumption led me to prepare a response in my mind. As soon as the thought entered my mind, I would stop listening and wait for the other person to finish talking. I literally wouldn’t hear any more words, and sometimes I would even jump in before they had finished

I’ve since realized that there is great pleasure in simply listening with the knowledge that I don’t need to respond. If I pause to think, and I say “hmm, that’s interesting” after the other person has spoken, that is something that is respected. Also, often if I pause for a little while, the other person will pick up again and–if it’s a challenge we’re working on–they might come to the solution by themselves. It’s much more powerful if they find the solution, than if I come up with it.

Ask lots of thoughtful questions

If it is indeed my turn to talk, I try to avoid “giving advice” or “stating my opinion” for as long as I possibly can. Instead, I ask questions based on the previous thing the other person just said. I listen very carefully and then once it is my turn, I simply respond with a genuine question of something I’m interested in based on the topic, but which he didn’t quite cover or for which I’d love to hear more detail.

If I have an idea to help the other person, I try to always present it as a question. I aim to guide them to my idea through questions. This means that if they reach the same idea and it’s the right thing for them, it will be much more ingrained and they will be much more likely to have determination to follow through.

Be open to whatever path the conversation takes

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This final point is the one which I think has been the most powerful recent discovery for me. I’ve realized that if I simply sit, feel no need to respond, and focus on hearing every word and learning quickly about the other person’s context, then very often the conversation will go down a whole new path than the “initial thought” I had which I used to respond with or jump in and cut the conversation off with.

This is amazing, because I often learn so much. I get to walk down a whole new area of understanding, which I haven’t experienced, rather than just respond based on my experience, which I’ve already gained. The biggest bonus I find is when I can help the other person come up with a better solution suited to their context, by listening and asking questions. This is often a solution I never would have thought of based on my own context.

Do you ever catch yourself having a response in mind and struggling to listen to the other person? I’d love to hear your thoughts and experiences on the topic of context.